The rise and fall of Esprit, SF’s coolest clothing brand

In 1991, San Francisco clothing brand Esprit sent a note to 200,000 young people with a simple question: “What would you do to make the world better?”

They turned the responses into a controversial ad campaign that ran on MTV and 11 other channels, giving teens the thrill of being heard and scandalizing their parents.

“Give back the land stolen from Native Americans,” one ad demanded. “I would distribute condoms in every high school in America,” read another. “I’d keep a woman’s right to choose, unless George Bush is free to babysit.”

In a country still grappling with the AIDS crisis, the Rodney King riots and the Gulf War, the “What Would You Do” campaign (featuring a young Gwyneth Paltrow) would turn out to be the brand’s biggest and most remembered, pushing boundaries and bringing San Francisco cool to the masses.

Esprit appealed to the youth with a message of lefty, post-racial harmony. Wild prints, bright colors and baggy silhouettes reigned. Their tote bags and T-shirts hung from all the coolest shoulders, adorning fashion plates with the legendary Esprit logo. With the logo’s omnipresence at the time, it may as well have been Supreme for the teens of the late ’80s and early ’90s.

The brand’s idiosyncratic, publicly forward-thinking co-owners, Susie and Doug Tompkins, were at least as vital to the brand’s image as the clothes and the ads. The couple seemed to personify the Esprit ethos: Susie would later become a prominent Democratic donor and activist, while Doug would go on to be one of the greatest environmental stewards of all time.

But underneath the splashy magazine profiles and heavy-handed political messaging lies another tale. It’s one of San Francisco corporate excess and office trampolines. By the mid-’90s, mirroring the rest of Boomer culture, the Bay Area hippies had fully transformed into take-no-prisoners capitalists, complete with brutal corporate takeovers and tumultuous divorces.

What began as a humble dress shop founded by two women operating out of a Broadway showroom ballooned into a multinational conglomerate worth $800 million at its height, before the decades to come hollowed out the brand — leaving its place in America as a relic in vintage shops and the imaginations of Gen X kids.

‘Plain janes in name only’

A 1968 ad for Plain Jane.

A 1968 ad for Plain Jane.

San Francisco Chronicle / Archival

The story of Esprit began with San Francisco’s Summer of Love in the rearview, when two 20-something friends decided to make dresses they actually wanted to wear. In 1968, Susie Tompkins and Jane Tise called their new company Plain Jane and began selling dresses to local boutiques out of the back of a Volkswagen Bus. 

Soon, Tompkins’ husband, Doug, joined the venture, using $50,000 from the sale of their outdoor apparel shop — a little place called The North Face — to cover a garment factory producing their designs in lots of 100.

The Plain Jane operation was spare. Susie Tompkins and Tise were in charge of packaging, and Doug Tompkins ran the business side of the company. Even when they convinced department stores like Joseph Magnin to stock their goods in-store and host pop-ups, they kept the company, hiring just two more people: Allen Schwartz for sales and Duncan Dwelle for operations. Both would later become key company shareholders.

Their dresses were cute and trendy — as an early ad said, “plain janes in name only.” Their style drew both from San Francisco’s stoned, nonchalant hippie culture as it did from the everyday fashions of the 1930s and 1940s, with lots of florals and what San Francisco Examiner fashion critic Maureen Kirby called “LOL,” or little old lady, prints.

A photo of Jane Tise, left, and Susie Tompkins at their Plain Jane showroom in San Francisco.

A photo of Jane Tise, left, and Susie Tompkins at their Plain Jane showroom in San Francisco.

San Francisco Examiner / Archival

The simplicity of their designs went against the ethos of many other dress designers of the era, such as Oscar de la Renta and Leo Narducci, who were playing with the same Depression-era nostalgia but refracted it through the lens of maximalism, with splendorous bell sleeves and lots of taffeta and silk.

That same aversion to largesse was reflected by the tiny showroom they went on to open, which stood in between two “topless sideshows,” Kirby said at the time.

“We don’t want to be a giant company,” the pair told Kirby in an interview just months after the brand launched. “We want to contain our size, and just grow a little with each collection.” 

‘A very aggressive individual’

A 1975 legal notice in the San Francisco Examiner.

A 1975 legal notice in the San Francisco Examiner.

San Francisco Examiner / Archival

Despite the aversion to excess, by 1970, Plain Jane was raking in a healthy amount of money — about $2 million in sales — allowing them to move their headquarters to the rapidly gentrifying Potrero Hill neighborhood. With this move came a new name, Esprit de Corp, which consolidated the many brands they were manufacturing under at the time. 

Doug had spent four to six months a year in the late ’60s and early ’70s kayaking and trekking around the great outdoors, but now he became actively involved in the company, including commissioning the nearby Jung Sai garment factory to make clothes exclusively for Esprit de Corp. 

Conditions in the factory were a far cry from the utopian ideals of the hippie founders. In 1974, factory workers struck, alleging poor working conditions, including delayed pay and racist treatment. Among one of the more obscene restrictions Doug had imposed was forcing its 135 workers to ration toilet paper at a rate of two rolls a day, according to Harvey Dong, an Asian American studies lecturer at UC Berkeley.

“On the strike lines in front of the main Esprit de Corp plant east of Potrero Hill, White female models, dressed stylishly in the latest fashions, walked through the picket lines of immigrant Chinese women production workers,” Dong wrote in the San Francisco historical anthology “Ten Years That Shook the City.”

Unable to just ignore the unionization efforts, Doug Tompkins responded by locking the workers out of the factory. He repeatedly got police to arrest workers. But the pressure, instead, intensified the strike, becoming one of the first major union strikes by Chinese immigrant women in San Francisco and in the country. 

Freelance researcher and historian Bud Theisen told SFGATE that Tompkins and other executives repeatedly stumbled while bargaining with the union, including “telling the union that he planned to move his sewing work to Hong Kong for better prices, which is a major mistake, as that’s illegal when dealing with a union,” Theisen wrote in an email.

In December 1975, the Department of Labor forced Tompkins to pay back wages to their laborers. But the victory was brief; months of striking had demoralized the workers, and a faulty union contract guaranteed that Tompkins came out on top.

‘No detail is small’

A 1985 photo of Doug Tompkins with Esprit art director Tamotsu Yagi.

A 1985 photo of Doug Tompkins with Esprit art director Tamotsu Yagi.

Corbis/Corbis/VCG via Getty Images

Disaster struck on the evening of Jan. 31, 1976, when a fire decimated the Esprit de Corp headquarters.

Firefighters combating the blaze told the San Francisco Chronicle that “that’s not the way buildings normally burn,” implying the fire was arson. 

According to Jonathan Franklin’s biography of Doug Tompkins, “A Wild Idea,” Doug responded by weeping for an hour. Then he moved on. 

John Casado, the designer responsible for Esprit’s iconic logo, described Doug as “a very aggressive individual” in an interview with SFGATE. “He was going to challenge you on everything you did, if he, if he didn’t know you, let me put it that way,” Casado said, calling from his home in SoMa.

Tompkins was as exacting and single-minded at home as he was at work, Franklin wrote, to the point where Franklin wrote that Tompkins “decorated [his daughters’] rooms the way he wanted their rooms to be — all gray and white.” 

A sign posted in the Esprit offices exemplified this vision clearly: “No detail is small.”

Casado described his relationship with Doug as intense, perhaps even confrontational. 

“​​You could ask other people, and 50% of them would say, ‘I did not like working with Doug,’ and the other 50% of the people … would say, ‘I loved working with Doug.’ And that really defined what your personality was.”

Shortly after the fire, around 1977 or 1978, Doug Tompkins staged what Thiesen effectively described as a “coup,” ousting Tise, Schwartz and Dwelle — the founding members of Esprit, who had worked so closely together in that little Broadway showroom — by buying out all their company shares.

(Tise stayed on as a designer for a few more years, despite selling her shares to Tompkins. In 1985, Susie Tompkins told the Examiner that she and Doug were still on good terms with her, though she’s done little press since then.)

In the wake of the takeover, the Tompkinses dropped the “de Corp” from Esprit, the beginning of its ascent to the juggernaut years. 

‘The biggest trend in teen fashion’

Susie Tompkins with Esprit designers Karen Johnson and Doreen Chen, circa 1985.

Susie Tompkins with Esprit designers Karen Johnson and Doreen Chen, circa 1985.

Roger Ressmeyer/Corbis/VCG via Getty Images

Who deserves credit for Esprit’s success depends on your tolerance for the narrative of the male genius. 

Oliviero Toscani, the boundary-pushing photographer largely responsible for reinventing Esprit’s public image, dismissed Susie Tompkins’ clothing in an interview with brand consultant Bertrand Pellegrin from 2017.

“She would just go to Europe and copy [designs],” he told Pellegrin.

It was Toscani, Casado and Doug who revolutionized the brand and brought it to new heights, Pellegrin argued.

Toscani spearheaded the brand’s new whimsical and racially diverse ad campaigns. In something of a precursor to the Instagram and TikTok fashion influencers peddling false reality, the ads professed to feature “real people,” who just happened to be slim and beautiful. (Toscani also designed the colorful, post-racial aesthetic of early ’90s Benetton ads.)

Esprit opened new stores with a plasticine, elegantly juvenile look created by the legendary Memphis Group designer Ettore Sottsass. The company even redesigned the offices, adorning an open floor plan space with artisan furniture and handcrafted Amish quilts. Office workers were treated to perks and amenities that would make a techie blush, including a company gym, a supply of organic fruits and juices and in-office talks from Gloria Steinem and other intellectual luminaries. They even had a company trampoline.

“Employees have gone white-water rafting in India, down the Zambezi in a kayak, and on a river expedition to Peru,” read one Universal Press Syndicate article from 1984.

But the creatives behind the brand had little respect for the products they were selling. Toscani despised the clothes. Even Casado told SFGATE that his inspiration for the sparse, thin-lined logo was based on his perception that Esprit de Corp sold “inexpensive, throwaway kind of stuff.”

“It gave me the impression of things being made in China, very inexpensively, disposable, etc.,” he told SFGATE. (By removing the “backbone” of the “E,” he reasoned, the logo looked like it would be stenciled “on a box that’s going to be shipped overseas.”)

But none of that mattered. The simple days of Plain Jane were long gone. In its wake was a brand channeling playful excess with a side of youth-obsessed California chic.

“Esprit fashions are probably the biggest trend in teen fashion,” wrote one 17-year-old in a 1984 article for the San Francisco Examiner, who documented her purchases at the time — “a white corduroy mini-skirt … a red three-quarter length fur blend sweater … and a white striped canvas purse.”  

By 1989, at its peak commercial presence in the U.S., Esprit had 80 stores and outlet shops nationwide, not to mention the countless department stores where Esprit was sold.

From the outside, everything was on the upswing. But on the inside, the company was at war with itself.

‘A challenge for us’

A 1984 recruiting ad posted in the San Francisco Examiner.

A 1984 recruiting ad posted in the San Francisco Examiner.

San Francisco Examiner / Archival

Esprit posted its first-ever losses in 1987, a stressor that would break the already-fracturing relationship between Doug and Susie Tompkins. By this point, a nearly two-decade run of nonstop growth had stalled. The two blamed each other; outsiders blamed the two of them.

The two very publicly fought over who would take the company over. Three new directors, one after another, came in to try and quell these tensions. For a while, it seemed that Doug would helm Esprit for good, with Goldman Sachs investors offering up Susie’s shares for $350 million. They divorced in 1988, splitting their Amish quilts equally.

At some points, the tension would veer into the absurd; sometimes Doug and Susie would even shoot competing ads, according to Esprit’s Europe branch head Peter Buckley.

With no one stable at the helm, cracks began to show. The quality of the goods went to the gutter. Even when the fashion cycle moved on to off-duty model chic and Kurt Cobain and hip-hop, Esprit kept churning out print-heavy, neon-glow clothes.

But in 1990, when Goldman Sachs backed out, Susie emerged as the victor. (She was something of a sore winner, according to Franklin, who claimed Susie called Doug a “malignant narcissist” with an army of yes-men surrounding him.) 

Susie tried to resuscitate the bloated brand with a 1992 collection called “Ecollection,” an environmentally-minded line with organic cotton and wool. It flopped with their primary demographic of teenyboppers. Her next effort, the Susie Tompkins Signature Line, flopped too, with critics calling it drab, muddled, a far cry from their playful roots.

The line “was such a shock to everybody,” one New York fashion analyst told SF Weekly. “There were dowdy housedresses, dark colors.”

Even the $8 million “What Would You Do?” campaign didn’t move the needle for sales. A revolving door of CEOs came and went. The media stopped covering it as a bohemian brand from San Francisco. It became just another fading clothing monolith.

A 1996 San Francisco Examiner photo of then-Esprit CEO Jay Margolis.

A 1996 San Francisco Examiner photo of then-Esprit CEO Jay Margolis.

San Francisco Examiner / Archival

CEO Jay Margolis was appointed in 1996, moved the headquarters to Los Angeles and banned every member of the Tompkins family from the building — including Susie. 

“It’s still a challenge for us every day to get back to what Esprit is, to fine-tune that,” Margolis told the Los Angeles Times in 1997.

‘I outgrew Doug, he outgrew me’

Despite the unceremonious ousting, Susie did just fine for herself, marrying real estate mogul Mark Buell and becoming a major Democratic donor. A 1997 profile in SF Weekly revealed that she was interviewed by the FBI over White House campaign solicitations, because she and then-President Bill Clinton had gotten dinner just a few weeks before.

“I outgrew Doug, he outgrew me,” Buell told SF Weekly in 1997. “It just was a time that we needed to get on with our lives.”

As for Doug, he abandoned all pretenses of remaining in the business world and instead became an ecological hero. He bought nearly 800,000 acres of land in Chile, and with former Patagonia CEO Kristine McDivitt, whom he married in 1993, transformed the acreage into the nature preserve Pumalin Park, which he eventually gifted to the country itself.

He died of hypothermia in 2015, following a kayaking accident in Chile.

Shoppers pass an Esprit clothing store March 26, 2005, in Munich, Germany.

Shoppers pass an Esprit clothing store March 26, 2005, in Munich, Germany.

Sean Gallup/Getty Images

These days, Esprit is a shadow of its former self, operating primarily in Europe and Asia. And yet the brand left a deep mark on American fashion. Boundary-testing designers such as Opening Ceremony’s Humberto Leon and Carol Lim cite Esprit as an inspiration, a brand they proclaimed to be at the vanguard of “mainstream American fashion” in the ’80s and ’90s. Opening Ceremony even launched a capsule collection with Esprit in 2017, the retro stylings melded with late-2010s trends.

“They were doing things no other brands were doing at the time, but have become the norm today,” Opening Ceremony co-founder Lim told Harper’s Bazaar. “… Esprit had a point of view and people wanted to be a part of that, so you were proud to wear the sweatshirt or carry the tote.”

Nostalgia has a funny way of obscuring flaws. Sure, the Esprit that we remember now is all ’80s California youth and vibrancy, but the reality is contradictory, imperfect and far more compelling — with environmentalists becoming tycoons and then back again, their socially conscious exterior belying the stifling of unionization efforts. 

In the end, Doug Tompkins may have been right. The lasting impact of Esprit was not the clothes or the controversies, but the image that it sold.